New flights from 3 US cities to the lesser-known Caribbean paradise

Take it from someone who just visited St. Lucia for the first time, every island certainly is not a stone’s throw away.

Proximity is one of the main reasons why islands like Jamaica and the Bahamas are so hugely popular, and so is Cuba If it wasn’t, well, you know…

Lost in the shadows of the more familiar names are sunny paradises that are perfect for a winter getaway, as much of the US mainland will be covered in snow, or at least endure chattering weather.

One such place is much more popular with our boys ‘across the pond’, given its status as a British territory – but no, we’re not talking about the British Virgin Islands.

A lesser-known airline is ready to take off in one of the Caribbean’s last remaining hidden gems, with crowd-free white-sand beaches, flashy beachfront resorts and a reputation as one of the Caribbean’s safest destinations for Americans looking for an adventure without the same regurgitated route.

A trio of busy airports will welcome three of only four flights from the US this December – the perfect time to escape not only the frigid holiday weather, but also the dreaded family gatherings.

BermudAir launches 3 new flights to Anguilla 🇦🇮

As it stands, American Airlines has long been the only airline serving Anguilla from the US

Offering weekly flights from Miami (MIA), with the addition of BermudAir’s new flights in the coming months, travelers will soon have four direct options for reaching this oasis on the map.

So who are the lucky winners who can escape the winter cold?

1) Boston:

If you thought you were going to Boston and thought you would start a new life, your opinion may change once the frigid temperatures of December arrive.

Of course, have a beer and something Cracker Jacks at Fenway during the summer, Boston sounds great, but once you get into the middle of the holiday season and the calendar change, the Caribbean will definitely be living rent-free in your mind.

BermudAir’s first new flight to Anguilla (AXA) will depart from Boston (BOS). December 17, 2025 on Wednesday and Saturday.

2) Newark:

This is no insult to one of New Jersey’s most populous cities, but people here aren’t sticking to the Jersey side in favor of the bright lights of New York.

Although the attraction only lasts so long before hordes of tourists trickle in to experience the magic of the “Big Apple” as a winter wonderland.

Being one of New York’s three major airports, you’ll see many ‘snowbirds’ flocking to its sun-drenched shores, and now another exciting option has been added to the mix.

BermudAir will launch the first flight from Newark to Anguilla December 18, 2025 on every Thursday and Sunday.

3)Baltimore:

Baltimore may be the Northeast’s surprising new tourist draw, especially for foodies, but scarfing down delicious crabs isn’t enough of a reason to stay in town and have to shovel out your driveway every morning.

Or maybe another Sunday of disappointing Ravens football will get you ready to get out of dodge.

Marylanders will soon have the chance to easily escape to Anguilla from Baltimore (BWI), which is scheduled to launch December 19, 2025 on Friday and Monday.

Why visit Anguilla for winter sun?

Even though the kids are back to school and the adults have maxed out their PTO over the summer, many Caribbean places can still be busy.

Anguilla is a rare place where there are little to no worries.

In addition to open beaches, you can enjoy relaxed luxury with phenomenal resorts to choose from. At the top of the list is of course the Four Seasons Resort and Residences Anguilla at a premium price tag with a comma.

For those on a tight budget: Shoal Bay Villa is a luxurious coastal retreat along Anguilla’s popular Shoal Bay, laden with soft white sand, swaying palms and a serene stretch of calm turquoise water.

Although small, Anguilla does not feel overdeveloped. There are plenty of secluded places where you can find your own piece of paradise, and now it’s easier than ever to get to it.

Moreover, according to Travel + LeisureAnguilla was recently mentioned the safest destination in the Caribbean.

The BermudAir experience

Bermuda-based BermadAir has only been zooming through the clouds for a few years, but has expanded its portfolio impressively in a fairly short time.

And so far so good in beating the legend of the Bermuda Triangle!

Don’t expect spacious Dreamliners or first-class amenities; the above flights will be operated with a fleet of smaller ones Embraer jets.

BermudAir does offer an entertainment system (via your own device), free drinks, and is not as strict as some US budget airlines, offering free carry-on bags regardless of your class.

As they continued to grow, the little-known airline was crowned the 7th best airline throughout the Caribbean by 2025.

Sam Sears

Sam, our lead writer and San Diego-based journalist, has visited 36 countries and written more than 1,000 articles with an emphasis on sharing his own travel experiences and highlighting lesser-known gems.